Tricholomic acid - Misplaced Pages

Tricholomic acid
Names

IUPAC name (2S)-2-Amino-2-acetic acid
Other names α-Cycloglutamate; α-Amino-3-oxo-5-isoxazolidineacetic acid
Identifiers
CAS Number	2644-49-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9690
ChEMBL	ChEMBL260328
ChemSpider	390188
KEGG	C08298
PubChem CID	441456
CompTox Dashboard (EPA)	DTXSID80949327
InChI InChI=1S/C5H8N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h2,4H,1,6H2,(H,7,8)(H,9,10)/t2-,4-/m0/s1Key: NTHMUJMQOXQYBR-OKKQSCSOSA-N
SMILES C1(ONC1=O)(C(=O)O)N
Properties
Chemical formula	C₅H₈N₂O₄
Molar mass	160.129 g·mol
Melting point	207 °C (405 °F; 480 K) (decomp.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Tricholomic acid is a non-proteinogenic amino acid found in some mushrooms, including Tricholoma muscarium. It has a chemical structure similar to glutamic acid, hence the synonym cycloglutamate, and it interacts with glutamate receptors. Because glutamate receptors are thought to be responsible for the reception of umami taste, tricholomic acid and close analogs have been investigated as flavor enhancers.

References

^ Takemoto, Tsunematsu; Nakajima, Tadashi (1964). "Studies on the Constituents of Indigenous Fungi. I". Yakugaku Zasshi. 84 (12): 1183–1186. doi:10.1248/yakushi1947.84.12_1183. PMID 14266548.
Tamborini, Lucia; Mastronardi, Federica; Lo Presti, Leonardo; Nielsen, Birgitte; De Micheli, Carlo; Conti, Paola; Pinto, Andrea (2017). "Synthesis of L-Tricholomic Acid Analogues and Pharmacological Characterization at Ionotropic Glutamate Receptors". ChemistrySelect. 2 (31): 10295. doi:10.1002/slct.201702154. hdl:2434/528800.
Kuninaka, Akira (1969). "Recent Studies of 5′-Nucleotides as New Flavor Enhancers". Flavor Chemistry. Advances in Chemistry. 56: 261–274. doi:10.1021/ba-1966-0056.ch015. ISBN 0-8412-0057-2.